GB1174780A - 01beta-Hydroxy-12alpha-Bromo-16alpha-Methyl-5beta-Pregnanes - Google Patents
01beta-Hydroxy-12alpha-Bromo-16alpha-Methyl-5beta-PregnanesInfo
- Publication number
- GB1174780A GB1174780A GB55738/66A GB5573866A GB1174780A GB 1174780 A GB1174780 A GB 1174780A GB 55738/66 A GB55738/66 A GB 55738/66A GB 5573866 A GB5573866 A GB 5573866A GB 1174780 A GB1174780 A GB 1174780A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- dione
- prepared
- bromo
- dihydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XMRPGKVKISIQBV-UHFFFAOYSA-N (+-)-5- Pregnane-3,20-dione Natural products C1CC2CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 XMRPGKVKISIQBV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- RSRDWHPVTMQUGZ-OZIWPBGVSA-N 1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RSRDWHPVTMQUGZ-OZIWPBGVSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical compound BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,174,780. 12α-Bromo-16α-methyl-5#-preg nan-11#-ols. E. R. SQUIBB & SONS Inc. 13 Dec., 1966 [22 Dec., 1965], No. 55738/66. Heading C2V. The invention comprises compounds of formula wherein Y is H or Br and Z is H, OH or acyloxy. The compounds wherein Y is Br are prepared by bromination of the compounds wherein Y is H, and the latter are prepared from the corresponding 11,12-unsubstituted-11-enes by reaction with an N-bromo-amide or -imide. 16α - Methyl - 5# - pregn - 11 - ene - 3,20- dione (II) is prepared by the sequence: 16α- methyl - 3α,12α - dihydroxy - 5# - pregnan - 20- one (III) # 16α - methyl - 12α - hydroxy - 5#- pregnane - 3,20 - dione # 16α - methyl - 12α- tosyloxy - 5# - pregnane - 3,20 - dione # II. 16α - Methyl - 21 - acetoxy - 5# - pregn - 11- ene - 3,20 - dione (IV) is prepared by the sequence: III # 3α,12α - dihydroxy - 16α- methyl - 21 - bromo - 5# - pregnan - 20 - one (V) # 3α,12α - dihydroxy - 16α - methyl - 21 - iodo- 5# - pregnan - 20 - one # 3α,12α - dihydroxy- 16α - methyl - 21 - acetoxy - 5# - pregnen - 20 - one # 12α - hydroxy - 16α - methyl - 21 - acetoxy- 5# - pregnane - 3,20 - dione -> 12α - tosyloxy- 16α - methyl - 21 - acetoxy - 5# - pregnane - 3,20- dione # IV. 3α,12α,21 - Trihydroxy - 16α - methyl - 5# pregnan-20-one is prepared by hydrolysis of V. Compound III is prepared from 3α,12α- diacetoxy - 5# - pregn - 16 - en - 20 - one either directly or via 3α,12α - dihydroxy - 5# - pregn- 16-en-20-one.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51574765A | 1965-12-22 | 1965-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1174780A true GB1174780A (en) | 1969-12-17 |
Family
ID=24052580
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB55738/66A Expired GB1174780A (en) | 1965-12-22 | 1966-12-13 | 01beta-Hydroxy-12alpha-Bromo-16alpha-Methyl-5beta-Pregnanes |
| GB2987569A Expired GB1179547A (en) | 1965-12-22 | 1966-12-13 | 01beta,12beta-Oxido-16alpha-Methyl-Pregnenes |
| GB2956069A Expired GB1179546A (en) | 1965-12-22 | 1966-12-13 | 01-Oxygenated-12alpha-Halo-16alpha-Methyl-Pregnenes |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2987569A Expired GB1179547A (en) | 1965-12-22 | 1966-12-13 | 01beta,12beta-Oxido-16alpha-Methyl-Pregnenes |
| GB2956069A Expired GB1179546A (en) | 1965-12-22 | 1966-12-13 | 01-Oxygenated-12alpha-Halo-16alpha-Methyl-Pregnenes |
Country Status (6)
| Country | Link |
|---|---|
| BR (1) | BR6685572D0 (en) |
| CH (1) | CH481075A (en) |
| DE (1) | DE1593480A1 (en) |
| FR (2) | FR1506008A (en) |
| GB (3) | GB1174780A (en) |
| NL (1) | NL6617943A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2632678C2 (en) * | 1976-07-16 | 1986-02-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 6α-Fluoro-12α-Halo-Corticoids and Process for Their Preparation |
-
1966
- 1966-12-13 GB GB55738/66A patent/GB1174780A/en not_active Expired
- 1966-12-13 GB GB2987569A patent/GB1179547A/en not_active Expired
- 1966-12-13 GB GB2956069A patent/GB1179546A/en not_active Expired
- 1966-12-21 NL NL6617943A patent/NL6617943A/xx unknown
- 1966-12-21 BR BR18557266A patent/BR6685572D0/en unknown
- 1966-12-22 CH CH1850866A patent/CH481075A/en not_active IP Right Cessation
- 1966-12-22 FR FR88569A patent/FR1506008A/en not_active Expired
- 1966-12-22 DE DE19661593480 patent/DE1593480A1/en active Pending
-
1967
- 1967-03-21 FR FR99664A patent/FR7021M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR6685572D0 (en) | 1973-12-27 |
| GB1179547A (en) | 1970-01-28 |
| NL6617943A (en) | 1967-06-23 |
| FR7021M (en) | 1969-06-09 |
| DE1593480A1 (en) | 1970-10-22 |
| CH481075A (en) | 1969-11-15 |
| FR1506008A (en) | 1967-12-15 |
| GB1179546A (en) | 1970-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |